For many fighters, the hardest battle is not in the ring but knowing when to walk away.

History is littered with boxers who could not resist one more shot, one more fight, one last chance to silence the doubts.

Olympic gold medallist and former two-time IBF super-middleweight champion James DeGale is no different.

On Saturday in Manchester, the 39-year-old will step into one of the most brutal arenas in combat sports: bare-knuckle boxing.

He meets Australian Matt Floyd at the AO Arena, six years on from the punishing loss to Chris Eubank Jr that ended his career – a memory that still gnaws at him.

“The way I went out against Eubank, it plays in my head every day,” he says. “I want to go out with a good win and show people how injured I was.”

DeGale knows his decision will raise eyebrows but believes attention and redemption could pave the way back to traditional boxing.

“The last couple of years of my career I was riddled with injuries,” he tells BBC Sport.

“I need to right the wrong and have a couple more fights just to show how handicapped I was.”

Although world titles are behind him, DeGale feels the modern boxing landscape – shaped by crossover shows and influencer bouts – offers new opportunities.

“Boxing at the very top and winning world titles again, that’s done,” he says.

“But boxing has changed. There’s [YouTuber KSI’s promotional company] Misfits, shows in Qatar, money everywhere.

“Jake Paul, Darren Till, Ty Mitchell, KSI, Tommy Fury – there are so many people I can fight.”

DeGale made history as Britain’s first boxer to win both Olympic gold and a professional world title, capturing the IBF super-middleweight crown in 2015 and defending it against top names.

But injuries and underwhelming performances took their toll. Defeat by Caleb Truax in 2017 was salvaged by a messy rematch win, while the Eubank loss in 2019 felt final.

DeGale says towards the end of his career he discovered he was neurodivergent.

One in five people are neurodivergent, an umbrella term for the range of differences in how our brains function, which includes ADHD, autism, dyslexia and synesthesia among others.

“At the end of my career, I got diagnosed with severe ADHD. Proper ADHD,” DeGale says.

“It impacted me a lot. I used to worry about what people would think, what they would say.

“I was probably a bit mentally weak at that time.”

ADHD challenges vary from person to person, but they can include hyperactivity, impulsivity and difficulty regulating focus.

DeGale believes ADHD contributed to poor decisions he made, but with medication and experience, he now feels grounded.

“I didn’t want to take that year and a half out of the ring to repair and heal,” he says.

“I was too impatient. But I’ve been medicated for the past five years, and I’m in a very good place. I’ve learned how to deal with my ADHD.”

DeGale left boxing with his health intact and has no desire to fight into his 50s.

Yet a comeback still called to him and bare-knuckle offered a route.

“I had such a good career, people said, ‘James, leave it, you smashed it’. There weren’t many opportunities, but then this came up,” he says.

“This is a way to get attention. Come back in the most brutal sport in the world and put on a performance.”

His immediate task is Floyd, a Perth fighter with a 15-2 professional record and a past as a former gang member who served time in prison.

The fight headlines a card for Bare Knuckle Fighting Championship.

“It’s boxing but with no gloves,” DeGale explains.

“There are some different rules: when you’re in a clinch you can hold the back of their neck and punch.”

Preparation has meant adapting familiar routines. Sparring bare-knuckle would be too damaging, so he has leaned on experienced specialists to guide him.

“I’m training with bare-knuckle fighters giving me all kinds of tips. I’ve been strengthening my hand and forearm,” the Londoner says.

“You don’t realise how weak your hands are until you start punching the bag and pads bare-knuckle.”

DeGale knows this comeback is a gamble for a man who has already achieved so much.

But for a fighter whose career ended with regret, this “organised straightener”, as he puts it, might allow him to walk away on his own terms.